Description:Waterloo is a c. 1750-1760 two-story four-room plan Flemish bond brick house. The gable-front south elevation is distinguished by a carefully laid glazed header checkerboard pattern divided in half by a two-course beltcourse, while the east elevation has a glazed header diamond pattern. The main house rests on a partially excavated Flemish bond foundation that is marked by a molded watertable. The four Flemish bond walls are covered by a medium pitched asphalt shingle roof. Tall interior chimneys rise from each lateral wall. White stucco quoins embellish three major corners of the house which face the road: the northwest, the southwest, and the southeast. The pedimented gable-front cornice is decorated with rows of modillion blocks which also encircle the house. The fenestration is symmetrically planned, with a center door and flanking 4/4 sash windows. Jack arches top each window opening. Below each first floor window is a stuccoed brick skirting in the shape of an upside-down "U." The center entrance bay is distinguished by a four-light transom over the flush six-panel front door and a Corinthian columned porch with a roof top balustrade. The second floor is similarly arranged with a center door that opens onto a porch. Flanking the door are windows of 4/4 sash. Located to each side of the door is a pair of iron bars that are matched on the rear facade. The diagonal bars are used to hold the iron tie rods in place. Centered within the pediment is a single 4/4 sash window and a small round vent which has been filled in and stuccoed over. The four-room plan house retains a mixture of Georgian and Federal period woodwork. The twisted baluster stair in the hall is the most unusual feature. Extending to the east from the main block is a single-story frame hyphen which connects the 19th-century kitchen. Attached to the west side of the main block is a c. 1959 brick bedroom wing designed in imitation of the old house. Surrounding the house is a group of outbuildings including a c. 1840-1850 doctor's office, a five-car garage, a frame caretaker's house and a small pump house. The Waggaman-Riggin family cemetery is located on the eastern periphery of the landscaped area around the terraced lawn.

Significance:
Waterloo is architecturally significant for several reasons. First, it is one of five prominent pre-Revolutionary War plantation houses which survive in Somerset County. This collection of houses represents the extreme height in architectural achievement on the Eastern Shore of Maryland by the mid-18th century. Built c. 1750 this two-story Georgian-period brick house displays carefully laid glazed brick checkerboard and diamond patterns on fields of Flemish bond walls. Waterloo is the only house on the lower Eastern Shore to have bold quoins on the three principal corners. Waterloo is also a pivotal house in local design traditions, for it is the earliest example of a gable-front main elevation, an orientation that was widely used in the region during the following century. In addition, the four-room-plan house contains a mixture of Georgian and Federal period woodwork. The most noteworthy feature is the triple-flight twisted baluster stair; few examples of this design survive in Maryland. Henry Waggaman, for whom the house was built, figures prominently in the history of Somerset County as well as the state. He was one of the most distinguished land owners and merchants in his day, and he served as an elder of the Manokin Presbyterian Church. From 1750 until his death in 1760, he was a member of the Provincial Assembly of Maryland. During the 19th century the property was owned by several locally prominent families until 1864, when the farm was purchased by the county for an almshouse. The county retained ownership of the property until 1948.